Old Friends, With Benefits
by QueenOfArt
Summary: Regina Mills decides to catch up with her old friend Annalise Keating while she's in town for a conference. The ladies catch up, reminisce, and get closer... (Disclaimer: This is actually a crossover between OUAT & HTGAWM...I love Regina and I love Annalise Keating so I wanted to write a fic with them together.)


**(Disclaimer: This is actually a crossover between OUAT & HTGAWM...I love Regina and I love Annalise Keating so I wanted to write a fic with them together.)**

Backstory:

Annalise and Regina first met 15 yrs ago at "The Nation's Most Powerful Women" Conference, where powerful women from all walks of life attended: Lawyers, Politicians, Doctors, etc. Eve Rothlo also attended the conference that year, her and Annalise actually went together, as colleagues (Yes, Annalise was married to Sam at the time). It was like friendship at first sight, Annalise hit it off with Regina upon meeting, and became very close. After a long day of seminars, the two ladies, along with Eve, went out for drinks, got a lil tipsy and went back to their hotel. That night things got a lil wild, wild as in a threesome took place! The morning after, the ladies went their separate ways. Annalise and Regina kept in touch with each other over the years, through phonecalls, emails, and text messages, but they only saw each other three times in the last 15 yrs on brief occasions.

* * *

Annalise got a call last night from her old friend, Mayor Regina Mills, from the town of Storybrooke. Regina called to say she was in Philly for the weekend, and she wanted to meet and catch up, since it's been years they last saw each other; Annalise happily accepted her visit.

 _7:00 pm, there was a knock at Annalise's door._

"Regina Mills"

"Annalise Keating"

"Its been a long time, you look great!"

"So do you, you're keeping yourself up I see."

"Trying to", Annalise blushed. "Come on in, and have a seat."

Regina came inside and went to the living room.

"So, what brings you here to Philly?"

"I was in town for a Mayor's Conference, and I just wanted to catch up with my old friend, its been years you know."

"I know, you don't get out of Storybrooke often, so I count this as a privilege. How long are you in town?"

"I'll be leaving tomorrow night, I got a hotel room downtown."

"Cancel your reservations, you can stay here with me. My students are out for the summer, and Bonnie is not around much since we're on break, so I'm here by myself."

"Are you sure?", Regina asked.

"Positive", Annalise answered.

"Well great, let me grab my bag out the car, and I'll be right back to settle in."

"You can take the guest room, it's the first room to the right upstairs. I'll go cook us some dinner, and then we chat, catch up, and have a girls night in." Annalise was excited for some company, especially since the company was her good friend Regina.

"Sounds good!", Regina smiled.

* * *

A half hour later, Regina came down from the guest room all freshened up in her lounge clothes, a silk pajama set. Leave it to Regina to keep it classy and sophisticated at all times, she still hasn't changed.

"Well look at you Madam Mayor, it's only a home cooked meal, nothing special.", Annalise teased.

"What?, Regina grinned, "this is my lounge wear." "Something smells good, what did you cook?"

"I cooked a apple turnover casserole, I think you'll like it. I'm not very domestic, but when I have quests over I like to show some hospitality."

"Thank, I appreciate that, and its apples, so I know I'll like it."

"You're welcome. Lets take our food in the living room to eat, so we can be more comfortable."

The ladies went into the living room.

"What do you want to drink?" Are you still a red wine girl?", Annalise asked.

"I am, red wine will be fine. Is vodka still your drink of choice?"

"Of course it is." Annalise went to her bar and poured Regina a glass of wine, and her a shot of vodka. She came back, handed Regina her wine, then sat on the other end of the couch beside Regina.

"So How's Henry? I know he's probably all grown up by now, he was just a small boy the last time I saw him."

"Henry's great, Storybrooke's great, everything's great."

"You mean they haven't ran you out of town yet?"

"Oh please, they will never get rid of me, no matter how hard they try", Regina said smugly. Annalise laughed. "So how have you been since Sam died? Its been two years now right?"

"Yeah, I'm surprisingly well, just trying to keep my students in line. I have an unruly bunch this go round."

"I pity you".

"They're like the children I never wanted."

'Well at least they keep you company. Soooo, is there anybody keeping you company?", Regina asked slyly.

"What do you mean?", Annalise dumbfoundlingly questioned.

"You know what I'm talking about Annalise. Is there someone in your life? A love life."

"Do you count the dildo I fuck everynight?"

They both bust out laughing.

"Yeah, if it talks to you", quipped Regina. "But seriously, you're single now and a beautiful woman, there has to be someone knocking at your door."

"Truth be told, I ran them all away. I'm my own worst enemy."

"Them? As in more than one? You haven't been so lonely afterall. I wanna hear about them."

Annalise changed the subject. "No, Iet's talk about you. Are you still seeing the Sheriff?"

"Who, Graham? Thats old news"

"Or is it what's his name, Rumple?"

"Never! We're just friends, well, frenemies, besides, he's not my type. But don't change the subject, who is Annalise Keating seducing these days?"

Annalise sighed, "His name is Nate, he's a cop, he fucked my brains out, I ruined his life, now he's out of my life." She then downed her third shot. "Anything else?"

"Yea, go back to the fucking your brains out part"

"Regina..." Annalise threw pillow at her.

"Mmm, we have cops in common, but you said 'they', so who else is it?"

Annalise snickered, "You're gonna love this...Eve Rothlo."

"Wait, not thee Eve Rothlo?"

Annalise nodded, "Yep."

"I knew you two had history, but I didn't know she was back in the picture. I haven't seen her since that night we all_ , well, you know".

Annalise reminisced, "I remember that night like it was yesterday. 'Distinguished Women Gone Wild'. " The ladies laughed.

"She had a tongue on her, and knew how to use it", Regina reminisced.'

"Tell me about it." Annalise took another shot of her vodka.

"That conference was everything. After the seminar, we went to he bar, danced, then headed back to the room to have some fun. If those walls could talk".

Regina continued on, "And I can't forget about you Annalise, 'The Strap Queen'. You had me climbing up the walls, you both did. That's when I knew I had a thing for women too. Who knew a night of drinks could change a person."

They both were quiet for a minute, then Regina broke silence. "If your husband Sam knew what we were doing at that conference."

"Oh please, he probably was somewhere screwing one of his students."

"You're probably right. So back to Eve, you two been seeing each other?"

"Yes, she came back into my life when I called her to represent a friend of mine (she didn't name Nate). One thing led to another and feeling came back. We hooked up a few times, but nothing too serious (at least on my part, Annalise thought). But last year she moved to California to be with her new girlfriend. I haven't seen her since. We text here and there."

"I see. I can tell by the look in your eyes you love he."

Annalise knew Regina was right, "I don't know what love is anymore, but enough about me Madam Mayor, anyone in your life? And don't tell me no one, because look at you, I know men are lined up at your door, and women."

"Speaking of women, yes there is someone. We mainly just hook up more than anything. Her name is Emma Swan, Henry's birth mother. Crazy right?"

"One big happy family, huh?", Annalise teased.

"At first we couldn't stand each other, but dealing with brought us closer, now we can barely keep our hands off each other, even though we both see other people on the side."

"Damn, you're just as complicated and messy as I am."

"We're quite alike, two evil bitches." They laughed.

"Its ashame we live far apart. You're all the way in the damn forest, in the middle of nowhere.", Annalise told Regina.

"Hey, hey, hey, back off of Storybrooke, but imagine the fun we would have."

"Yeah, we would."

* * *

Annalise and Regina spent the next hour on the couch, laughing at themselves, telling stories, and catching up. The ladies learned they had alot in common, professional and personally, they really were enjoying each other's company. Once they settled down, they found themselves just staring at each other, the mood shifted, the atmosphere went from playful to intimate. Regina made the first move, she scooted closer to Annalise, while Annalise met her half way. They started to kiss, the soft pecks quickly turned to french kisses, with both tongues entering the other's mouth, exploring. Annalise cupped Reginas face to to kiss her deeper. Regina moaned with pleasure, and then broke the kiss, panting, coming up for air.

"Mmm, your kiss taste like chocolate...to match your smooth skin", Regina said, while rubbing Annalise's thigh.

"And your lips have the taste of a juicy apple. I'm tempted to find out if your lips down below taste the same?"

"Only one way to find out...", Regina replied seductively.

Annalise then took Regina's hand and led her up the stairs to her room...


End file.
